Molly the Cleaner

If you haven't read parts 1-3, you need to. There's nothing more boring for a reader than a recap and I won't be repeating Molly's and my ritual.

Molly and I had an arrangement that if I wasn't dressed in a robe or she brought our cups of tea still dressed in her leggings and sensible top, it meant we reverted to tea, chat and card or board games.

At our disparate ages and genders we had different reasons to 'not be on' and we'd agreed no questions would be asked. That had been the situation for the past week.

This day though, Molly had brought her own uniform. It consisted of a mid thigh length leather skirt. Nothing else. Her perky breasts were on full display and her long stiff nipples told a story of their own. She brought our tea and unconventionally served mine from her side of the coffee table.

As she set mine down she said, "Take your robe off please Mr Wilson." Her expression was a mixture of her usual youthful exuberance and confidence, expectant excitement and a little apprehension.

I raised an eyebrow at her 'impertinence' and her face broke out into a more relaxed cheeky smile. "I like to see you naked, Mr Wilson."

I did as requested. She remarked, "I haven't seen you like this before," referring to my flaccid state, "I'm glad you're like that today. I'll get to see you grow."

This was all far removed from our usual games. She sipped her tea and said, "I've got a few personal issues to talk to you about Mr Wilson. I know I can trust your discretion to protect my privacy and not discuss what I'm about to tell you with anybody else." I was wondering where this was going. We'd always had fun and this sounded serious. I nodded in agreement and smiled in a comforting way to encourage her.

"The first thing you should know is that, technically, I'm a virgin. I've had my cherry popped. I've had dildoes, vibrators and even fruit inside my pussy, but never a real live flesh and blood cock."

I nodded and hoped my facial expressions encouraged her to feel safe and open up. I've got a real soft spot for Molly, as well as a growing hard spot as my cock head emerged from its protective foreskin at the thought of what might be coming.

Molly dampened my cock's enthusiasm a little as she continued, "And I'd like to keep it that way for now. The thing is, I have a really strong need to be penetrated by a real live cock." I was a bit confused.

"You see, I've been watching a fair bit of anal porn lately," she now had my cock's full attention back as it started to grow and stiffen again. Molly watched it and giggled. I think that made her feel more relaxed than any nodding or facial expressions.

She continued, "It turns me on..... a lot. But most of what I've seen is really rough and abusive and that's not what I want."

I've learned enough about women in my 61 years to know that know was not the time to say anything but, "Go on."

"I want my first time to be with somebody who'll be gentle. Somebody with enough experience to introduce me to it in a way that I'll enjoy it."

Her slight pause was my invitation to contribute. "I think you're being really sensible in both respects, Molly. Most people's experience in losing their virginity isn't usually fantastic. They usually ponder on it for a long time, build great expectations and imagine a wonderful experience and when it happens it's often clumsy and forgettable."

"A first anal experience, just because of the nature of it, can be even worse or better depending on how it's handled."

She smiled widely, "I knew you'd understand Mr Wilson."

As I continued Molly's right hand toyed with her right nipple and her knees parted, affording me a lovely view up her skirt, showing me her pantiless pussy.

"I can tell you from experience that an anal deflowering can be an awful experience, but done the right way, can be a wonderful experience."

Molly was very enthusiastic, "Let's get started then!"

I was more hesitant, "Hang on a minute sweetie. There are some........ aids that I don't have on hand and we shouldn't rush it without them."

Molly giggled again and grabbed her bag. She emptied it onto the lounge beside her. "I've thought about that. Will these do?"

She had some vital equipment like lubricant and oil, some that could be helpful like some vibrators of varying sizes and some that weren't necessary like condoms and an anal bead wand that might be fun at a later time.

I said, "You're well prepared Molly. So, you're 100% certain about this then?"

She nodded and replied, "I'm absolutely sure. I'm really excited about it and very nervous at the same time, but you're the only person in the world I trust to do it Mr Wilson. I know you'll be gentle and try not to hurt me."

I felt a sense of pride in Molly's trust in me and responsibility to make sure I made her first anal experience one that would be memorable for her and make her want more. The last part of that had some selfish motivation, I have to say.

"Then let's go to the guest room and make use of the bed Molly. That will be more comfortable than our usual playground out here," I said as I stood up and held out my hand to take hers.

She quickly gathered her accoutrements and took my hand, which I squeezed to give her comfort in the knowledge she was safe in mine.

She upturned her bag on the bed to give me access to what I needed. "Let's get rid of this skirt first," as I unzipped it at the back and it fell from her slim hips, revealing her delectable butt.

How to describe it? I'd call it a bubble butt, without it being a Brazilian butt. More like a peach, her cheeks nicely round and sticking out a little more than you'd expect when you consider the shape of her hips. Her butt flesh is youthfully smooth and unblemished. It's firm without being tight. It has some 'wobble' in it and I love wobble in a woman.

I stroked that pretty arse with both hands and told her, "You have the most wonderful arse, Molly. It's my favourite part of you. Am I allowed to have a favourite?"

She giggled, a little embarrassed and said, "Yes."

I urged her onto the bed with my hands, so that she knelt on the edge. It was the perfect position and height for what was to come. I put two pillows on the floor to make life easier for my old knees.

I squeezed her cheeks and pulled them apart to reveal her starfish. It's also a work of art. Her arsehole like a small dot in the middle of identical and perfectly symmetrical, long puckers. It's spellbinding in its perfection.

In fact I was so spellbound, I almost didn't notice the polymer hoop protruding from her pussy. 'Clever girl', I thought. Having her Ben Wah balls in to add to her excitement and maybe distract her from any pain she might feel. Pain I intended to avoid with proper preparation.

I leaned forward and kissed Molly's puckered hole and as I kept my lips there, my tongue slid between them and against her tight hole. I felt her shiver as I did and a sigh escaped from her lips. I used my tongue to wet her with my saliva, the first part of her lubrication.

I reached around and took Molly's left hand, placing it on her left cheek and supporting her upper body so her head lowered comfortably to the bed. I reached for her right hand but had to search for it, because it was between her legs, fiddling with her toy and her clit. I placed it on her right cheek.

"Keep your cheeks pulled apart for me Lovely, while prepare you," I directed her. Her upper body lowering resulted in her arse raising a little and pushing out some more.

I put a small dollop of oil on my index finger and rubbed it gently around the entrance to Molly's arsehole. "How does that feel Molly?" I asked her.

"Mmm, it feels nice Mr Wilson. You'll take it slowly, won't you?" She till sounded excited but apprehensive.

"Of course I will sweetie. You just tell me if I'm going too fast or do anything that hurts too much. You might feel a little bit of pain at times, but it won't be too bad and it will go away quickly," I needed to keep her calm so she'd enjoy it and figured me talking her through what I was doing would help.

"I'm going to put a lot of oil on my finger and slowly push it inside you, to let you get used to it. As you know Molly, my fingers are fairly thin, so it shouldn't be too hard for you. Are you ok with that?"

She nodded and said, "Yes Mr Wilson. Thank you."

I oiled my finger and slowly pushed about half of it inside her tight arse. "I'll just leave it there for a while. Your sphincter muscle is very tight, but it can relax if you stay relaxed. It will get used to being opened a little and stop being so tight. Now I'm going to pour some oil on your entrance and my finger and I want you to tell me when your ready for the rest. Remember that my finger further down is a little bit thicker, but it won't stretch you as much as when I first pushed my finger in."

Molly's arsehole twitched at the feel of the oil and she surprised me by pushing back and impaling herself on my finger. She moaned and said, "That feels really good Mr Wilson. It doesn't hurt at all."

"Good girl," I said encouraging her. "Are you ready for a bit more?" She nodded.

"Now, if I pull my finger out and then try to put two in, your sphincter will tighten back up and pushing two in might hurt, so what I'm going to do is keep my pointer finger inside you and slowly push my other pointer finger in alongside is it. Are you ok with that?"

She nodded again and said, "Yes please Mr Wilson. I trust you and I want my arsehole to feel stretched." She now sounded less apprehensive and more keen.

I oiled my other finger and pushed half of its length inside her. I could feel her tight muscle protest a little, but then relax again.

I buried my second finger and Molly flinched. "That hurts, but it's a good hurt. Don't move. Fuck, I wish I could touch my pussy."

"Please feel free to Molly. Play with your pussy as much as you like, just keep yourself spread with one hand," I encouraged her, thinking 'Fuck, I wish I could touch my cock,' which was harder than Chinese arithmetic.

I let Molly have some fun until I felt her arsehole start to open and close as her orgasm approached. I didn't want her to cum until my cock was in her arse. I was happy to edge her though, to make that anal orgasm more explosive.

"Molly, I need you to grab your thinnest vibrator and the oil please." She knew she had to stop masturbating and do as I asked, because she was trusting me to take her anal virginity and she was enjoying it at this stage.

Her thinnest vibe was slightly thicker than my two fingers, but about 15cm long. "You can take your hand off your arse to do this. I need you to cover your vibrator with lots of oil and then hand it to me.

She did as I directed and held the vibrator so I could reach it. "Now spread yourself with the other hand. I'm going to remove one of my fingers and take the vibrator off you. Then I'm going to take my other finger out and immediately replace it with your vibrator. Are you OK with that?"

She was now so horny, she replied, "Oh god yesss. Do it to me."

I prepared myself to do it as quickly as possible. I managed to perform the manoeuvre in less than 2 seconds. Not bad for an old bloke. I had half of the vibrator inside Molly.

It was a thing of beauty to see her starfish clench onto the vibrator, trying to close more, but not able to. Another thing of beauty was to hear Molly grunt, groan and exclaim, "Ooh that hurts....... so good."

"You're doing really well Molly. How are do you feel? Do you think you'll be able to take something a little bigger?" as I pushed another inch or two inside her.

"It's good Mr Wilson, but I don't know how much thicker I can go. I can take it deeper, but I don't know about thicker," she replied and my reply was to push the full length of her vibrator into her arsehole.

"Let's just leave that there for a while to let you adjust, Molly. In the meantime, I'm a little hungry. Why don't you turn over on your back, while I hold this in and make sure your tight arse doesn't shoot it across the room.

She giggled at that. I love hearing her giggle and the double joy was that it meant everything was going as I planned. She flipped onto her back and her legs splayed naturally.

I bent and took Molly's clit between my lips and sucked it as I licked it. I took the end of the vibrator in my hand and pulled it in and out in short strokes and in a miracle of fine motor skills for an oldie, I hooked one of the fingers of the hand that was fucking her into the hoop of her Ben Wah balls.

Being fucked in her arse by the vibrator, having her balls jingling in her cunt and my mouth on her clit was bringing her towards orgasm very quickly. I wanted take her right to the edge without allowing her to cum. I judged just the right time to stop.

She was furious in a sexual way, but rather than complaining, she begged. "I want your dirty old cock in my arse Mr Wilson. Give it to me please......please!"

"Now isn't the time to rush things and spoil it sweet Molly. This is special. Hold the vibrator in for me," I told her, convincing her that this had gone well so far, so she should continue to trust my judgment.

Of course, she did as directed while I climbed on the bed, presenting her with the sight of my throbbing cock for the first time today. "If this is what you want in your arse, young lady, you'll need to prepare it properly."

I took the oil and dripped it along my length. She knew to use her free hand to lube my cock. As some of it soaked into my skin, I added more until it was super slippery. I noticed her smart phone on the bed.

"Hey Molly," I said as I handed it to her, "Not many people would be able to look back and watch their anal cherry being taken."

She smiled a wicked smile, wiped her hand on the bedsheets and took the phone. "For a dirty old man, you're not a bad thinker Mr Wilson. I bet you'd like to watch it too. I'll have to call you my filthy old man."

I climbed back to kneel on my pillows on the floor. "Spread your left cheek with your left hand so you can video with your right and I'll spread your right cheek." Everything was working perfectly. "Are you ready Molly?"

"Fuck my arse Mr Wilson. Put your fat cock in my tight arsehole and fuck it." I could see she had the light of her phone on and her vibrator was starting to slip out.

I used my right hand to position my cock and when the vibrator dropped to the floor, I saw the beautiful sight of her arsehole stay open. I immediately pushed just the head of my slippery cock inside her arse.

"Oh fuck, that feels so hot. It's so big." She was gagging for it. I only gave her a few seconds to adjust. I couldn't lose the moment and allow her arsehole to tighten again. I pushed my cock balls deep into her and held it there.

The look on her face was priceless. Her eyes and mouth were wide open in surprise and she seemed frozen, taking in what had just happened.

I noticed she'd dropped her phone and I picked it up and pointed it at our union. That seemed to bring her back. "I feel so full. It doesn't hurt. It feels fucking fantastic. Fuck my arse Mr Wilson, fuck my dirty arsehole!"

I knew it would be a mistake to go full on right now. I started fucking her with small strokes, each time pulling out just a little further. Her eyes remained wide open and looked directly into mine.

I could feel Molly's arse start to flutter. It was now or never. I started pounding her, withdrawing my cock to the tip and plunging it in until my balls slapped her arse cheeks and my pubic bone smashed against her clit. I could only imagine what her Ben Wah balls were doing.

Still staring into my eyes, Molly proclaimed, "Fuck my arse. Fuck it long and hard. Oh fuck, it feels so good. So good to be fucked by a real cock. So good to have my arse fucked."

Her hand went to her clit and her fingers flew back and forth across it. I felt Molly's arse completely loosen. So much I couldn't even feel it. I knew what was coming. Molly was. I slammed my cock into her and held on for dear life. I was determined her arse wouldn't spit my cock out when her orgasm arrived.

Her arse clamped down tight on my cock and her mouth opened wide. She couldn't talk. She just made gurgling noises as her arse fluttered on my cock. Then it happened.

Molly started squirting on me. She had to stop fiddling with her clit as her whole body contorted. Her juices sprayed me. One long squirt, like she was pissing and then shorter, but no less strong squirts.

"I'm going to cum in your arse Molly. I'm going to fill you up with my old, hot cream. Here it comes my lovely," I babbled.

Molly found her voice, "Yes Mr Wilson. Do it to me. Give me your spunk. Shoot it into my dirty arsehole."

As I began to pump my seed into her, Molly came again. Again spraying me with her pungent juice. We came together and it was so good. It might have been the best cum I'd ever experienced. Just so, so hot.

We lay there for what seemed like an eternity, trying to make the immense pleasure last. But my manhood did what manhoods do and my cock began to soften. I wanted to feel Molly's arsehole as I withdrew, while my cock was still reasonably hard.

As I did, Molly's arsehole farted a sex fart and then another and that was followed by my cum flowing out of it as her hole slowly closed shut.

I was sure then that our anal adventures wouldn't end there.